


I Think They Should Date

by hippohead



Category: Glee
Genre: AU, Coworkers!Klaine, Enemies to Lovers, Fluff, Humor, M/M, Vogue!Klaine, a slight:, but mostly it's just Kurt being stubborn, i never know how to tag things help, the tiniest bit of angst?
Language: English
Status: In-Progress
Published: 2020-10-06
Updated: 2020-10-06
Packaged: 2021-03-07 20:26:52
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,256
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26853673
Author URL: https://archiveofourown.org/users/hippohead/pseuds/hippohead
Summary: Kurt loves his job and he loves his boss, Isabelle. He also loves having weekends and time for his skincare regime and the ability to go on dates. So, when he sets Isabelle up with Arthur, one of their coworkers, it’s only because he’s desperate. Desperate enough to go to Blaine Anderson for help. And it was just supposed to be a fling; enough to distract Isabelle during the weekends and no more, but hearts don’t work like that. Hearts fall in love and hurt people and get broken. And sometimes, hearts start to belong to the person you really want to hate.Or, the (very loosely-based on) Set It Up (2018) Klaine AU
Relationships: Blaine Anderson/Kurt Hummel
Comments: 15
Kudos: 22





	1. Chapter 1

**Author's Note:**

> Ok. This is fine. I’m going to attempt my first multi-chapter here. I have a bunch written and all of it outlined, so I’m feeling optimistic about posting fairly regularly. Also, I have only seen this film once right when it first came out so my memory of it is hazy. I decided not to re-watch it so that this story could be its own thing, but still influenced by the film as a whole. But, yeah, there won’t be a lot of direct scenes or plots because I honestly can’t remember them? I do remember enjoying the film though, and thought this could be a fun situation to put our Kurt & Blaine in. This first chapter is more of a prologue, to set us up (get it?) for the story. I am nervous. Please enjoy. 

Kurt loved Isabelle, he really did. But he was just about ready to strangle her.

He was pretty sure he'd lose his job if he strangled his boss, though, so he refrained. Also, that would be murder, and as much as he loved _Chicago_ , he was almost certain there wouldn't be a singing Renee Zellweger or Catherine Zeta-Jones in prison.

This was the fourth weekend in a row he'd had to work the whole way through, on top of his usual full-time and long hours, and he was pretty sure if he didn't get a day off soon, he was going to break. Or snap. Or do something stupid, like quit. Which was crazy, because this was his dream job. Or it was the job before the job that led to his dream job. He was on the ladder, at least. 

Isabelle was hunched over her laptop, murmuring to herself, but Kurt had figured out almost two years ago that she wasn't actually saying anything coherent whenever she did that. More often than not, she was just making noise to make it feel like she was doing something, achieving something, getting somewhere. Kurt was sure that he knew Isabelle's habits and tricks more intimately than anyone else in the world. Part of the territory of being her right-hand man, he supposed.

The reason they were on their fourth consecutive weekend at the office was because Isabelle had been entrusted with the Autumn Showcase for the first time and she was spiraling. Kurt would never say that out loud - he and Isabelle were close, sure, but she was still his boss. And if she demanded that he spend every waking moment overpreparing for an event that was still six months away, well, he was going to do just that. Even if it meant biting his tongue about how highly-strung she had become and not pointing out that they were actually ahead of the insanely detailed schedule and timeline she had made Kurt create on day one. They were on track, the cogs turning and churning as they should be, and Kurt felt quietly confident that they were actually going to pull it all off really well. If Isabelle needed to panic anyway, today, and for a while longer, that was okay. But-

They've been here since eight in the morning.

And it was nearing dinner time, and Isabelle seemed just as settled at her desk as always. Kurt did wonder, sometimes, if it was legal for him to be working this much, but he'd sold his soul to Vogue five years ago and at this point, he would live in this building if Isabelle needed him to. But all of this didn't mean he wasn't desperate for some downtime - his skincare regime was being seriously neglected, and he kept falling asleep on the subway. 

"Are we- do you want me to order some dinner?"

He was trying to hint at the absurdity of the fact that they were still here at dinner time on a Sunday night, but that went entirely over Isabelle's head and she mumbled a, "That'd be great," in Kurt's general direction. He sighed, pulling out his phone to call the Thai place down the road, but he got distracted by a text message that he hadn't heard come through.

**Chandler (Record Store Guy)**  
_Gutted this weekend didn't work out - let me know if you have any free time next weekend?!_

Kurt sighed again. Chandler had seemed like a lot when they'd met but Kurt had been impressed at how forward he had been in asking him out and he hadn't been on a date in almost five months. The attention had felt nice so he'd given him his number which Chandler had used before Kurt had even left the store, and the pair had been trying to set up a date for a while now. Kurt was starting to wonder if trying to date at the moment was pointless, though, because he couldn't see the end of this working-all-the-time tunnel.

He clicked away from the message and dialed the Thai restaurant's number, placed an order, and went down to the lobby to pick it up once it arrived. It was nice to have a break from Isabelle's stressful office, even if it was just an elevator ride to tip the delivery guy. He set all of the food out on a table in the staffroom and then went to drag Isabelle away from her computer. 

When he walked through the door to her office, there was a loud, frustrated huff and Kurt watched her for a moment. He’d been so consumed by his own bitterness at being here that he hadn’t even noticed how tired Isabelle looked. She’d been working just as much as he had, maybe even more, putting everything into this project. He knew how important this was to her and to the company, and he felt a pang of guilt for his (hopefully mostly silent) sulking. It wasn’t always like this; normally things ran really smoothly, Kurt and Isabelle having formed a kinship and an understanding of one another that meant they were sometimes out the door a little early. All of Kurt’s friends at Vogue were jealous of him – Isabelle was known for being an incredibly generous and kind and lenient boss. 

She was all of those things, and more, but they were going to be working on this project for the next six months and if she intended on doing these sorts of hours the whole time – well, she was going to collapse. 

“Isabelle?” 

All she did was hum, but at least it was an acknowledgement. 

“The food’s here. Let’s have something to eat.” 

It took a little more convincing, but eventually they were sitting at the staffroom table with all of the options Kurt had ordered spread out around them. 

“This is great, Kurt. Thank you.” 

“You needed a break,” he smiled at her kindly, hoping she would let her brain stop whirring for five minutes while they ate. 

“I’m sorry I’ve been working us so hard these past few weeks. This is the first time they’ve put me in charge of the Autumn Showcase and it has to go perfectly.” 

Kurt nodded; he knew. She’d told him that constantly, consistently, her guilt causing her to over-explain. “I know.” And then, hoping to distract her with mindless information about their coworkers for a little while, he said, “Did you hear about Darian from Accounts?” 

“No, what about him?” Isabelle asked, mildly interested. 

Kurt continued on, “Well, Tina told me that he and his girlfriend broke up last week because she’s moving to Chicago.” Tina was Kurt’s friend who worked in Accounts with Darian and knew everything about everyone. Kurt wished he was stronger and didn’t indulge her gossipy habits but she’d call him on his extension line or run into him in the hallway and lower her voice in a way that felt special and included. He was powerless after that. And besides, she did always have an interesting story to tell. “Reckon I have a chance now?” 

Isabelle laughed because she knew he wasn’t serious and it was nice to hear the sound. It had been a while since the last time he had. 

“Hm,” Isabelle said, pretending to consider it, “You’d have better luck with Arthur from Editing. He’s bisexual.” 

Oh. Kurt didn’t know that, but that was cool. It was nice knowing there was an openly bisexual man running a department here. _Blaine’s_ department, his brain supplied rather unhelpfully. He told his brain to shut up. 

“Arthur’s not really my type,” Kurt shrugged. And that was true – he had long hair past his shoulders that he tended to wear tied back into a low bun, and he was too tall for Kurt’s taste. That was all very superficial, sure, but what can you do? 

Isabelle snorted, “Kurt, are you serious? That man was chiseled out of marble. You really wouldn’t?” And when Kurt shook his head, no, she rolled her eyes and said after her mouthful, “That’s crazy. I would let that man do whatever he wanted to me.” 

Kurt raised his eyebrows at his boss – were they really going there? Sure, they whispered about which models they thought were hot during shoots and they kept each other vaguely updated about their love lives the way coworkers who were friendly would, but talking about _chiseled_ and _I would let that man do whatever he wanted to me?_ That was more than he’d bargained for when he brought Darian up. 

“Oh, come on. You’ve never had a work crush before?” 

And that – that hit a little too close to home. Kurt tried to chuckle like her comment didn’t spin him, “Not really, no. Anyway, we should get back to work or else we’ll be here until we’re due in tomorrow.” 

Isabelle looked a little guilty at that, and he really didn’t mean for her to. Mostly, he was just trying to avoid having to think about work crushes. 

It was an hour later, both of them stuck back into planning and lists and colour swatches, when the idea wandered into his mind. At first, he dismissed it as ridiculous and outlandish, but then Chandler sent him another text and he looked at the clock. It was past ten on a Sunday night. 

Ridiculous, outlandish, sure. But he was going to give it his best shot. And if that meant he was going to have to think about work crushes - actually; _ex-_ work crushes, then so be it. Isabelle needed this. He desperately needed this. 

So, it’s decided. 

Tomorrow, he has to talk to Blaine Anderson. 


	2. Chapter 2

They had made it out of the building just before midnight, and Isabelle had hugged him and told him not to come in until after nine tomorrow. 

So, he's at work at half-eight. 

He spends the first few hours juggling showcase stuff and his normal workload, everybody and their dog coming to him with issues that had risen over the weekend because Isabelle was too busy to be asked. 

It was well past his usual lunch hour when he finally had a moment to breathe, break, be still for a moment longer than a handful of seconds. He’d eaten a salad quickly and had been pacing outside the editing department for at least half an hour. It was getting ridiculous and he’d already had to fend off questioning glances from coworkers as they walked past and saw him wringing his hands. He needed to just do it; to push through the door and look at him sitting behind his desk with his stupid hair perfectly styled and his stupid honey eyes perfectly swirling and do it, _say_ it. 

Pull the band-aid off. 

“Hey,” he hovered by the edge of Blaine’s desk and felt an insane bout of jealousy over the fact that it was bigger than his. Also, Kurt had been working here longer, so how did Blaine get a spot right by a window overlooking the Hudson? All Kurt had to look at was a conference room and a tacky indoor water fountain. There was no world in which that was fair. He couldn’t help it – his inner monologue always got petty when he thought about Blaine. Which he tried not to do. 

“Oh, hey, Kurt.” 

Blaine was smiling up at him in an interested and friendly way and god, it was so annoying. He had a desk with a view _and_ a personable nature. And one might say he had a great smile, too, one that made the rest of the room fall away and made you want to smile that great back, but not Kurt. All Kurt saw was smug and over-confident and _annoying._

He wanted to ask how Blaine knew his name. They’d talked exactly three times over the past two years, if you included the time Blaine had said, “Hi,” when they’d passed each other in the hallway and Kurt had barely nodded back. He was pretty sure Blaine had no idea who he was and that was part of the whole reason he hated Blaine. Blaine knowing his name unraveled that, so he chose to ignore it and barreled on with his plan. 

“Do you know if Arthur is single?” 

Blaine seemed to be taken off-guard by the question, but he regained his composure almost immediately and then raised his eyebrows, his smile turning into a grin, “Are you trying to date my boss, Kurt?” 

And there he went again, saying Kurt’s name as if he knew how to, was allowed to. He managed to swallow the tired sigh and instead set Blaine with a look he hoped said, _that’s cute. “_ No, Blaine, I am not trying to date your boss.” 

It looked like Blaine was assessing him, or assessing something about him, because he narrowed his eyes at Kurt before he seemed to settle on a decision, “He’s single, yeah. His wife divorced him a year ago.” 

Kurt exhaled happily, “Good. Perfect.” 

Blaine raised his eyebrows again and Kurt almost warned him that he was going to wrinkle early if he kept doing that, but then he remembered that he hated Blaine, and so he would let him ruin his skin out of spite. It became clear that the eyebrows were his input into the conversation, waiting for an answer, so Kurt rolled his eyes and spoke again. 

“I have a proposal for you. It involves your boss and my boss and I need your help to make it work.” 

Blaine leaned back in his chair, dissolving from professional to casual in the movement, and Kurt wondered what it was like to be able to melt that easily around an almost-stranger. “Okay. Consider me intrigued,” Blaine said. 

“Meet me in the lobby after work. There’s a nice bar a couple of blocks away, and I’ll explain more.” 

Blaine chuckled, “Are you trying to date _me,_ Kurt?” 

If he’d asked that question a year ago... well, his answer would have been very different. But it wasn’t a year ago, it was now, and he hated Blaine, so he set him with a cold, unimpressed stare, “Don’t flatter yourself.” 

“Wouldn’t dream of it,” Blaine said, and there was a joyfulness in his tone that made Kurt’s blood boil. 

He assumed that meant yes, so he stalked off back to his desk, annoyed that he’d have to spend time with Blaine tonight, but happy that he had the ball rolling on his plan. 

* * *

Blaine had been pleasant all night long and it was driving Kurt crazy. 

He’d been pleasant when Kurt had arrived half an hour late to meeting him in the lobby. He’d been pleasant on the walk over to the bar even though the cold was nippy and biting their faces. He’d been pleasant as he’d pulled a chair out for Kurt, and ordered both of their drinks at the bar. And he was still being pleasant now, and patient, too, as Kurt tried to explain the situation. 

“And I feel like I haven’t slept in months,” he finished. 

Kurt had barely looked at Blaine the whole time he’d rambled on about working late and weekends and the workload heading towards unbearable, but he looked up now. Blaine’s brows were knitted together in sympathy that Kurt didn’t want and his fingers were dancing a condensation pattern on his beer bottle. “That’s awful, Kurt. I know how crazy the place gets when it’s busy.” 

Kurt waved his hand dismissively. “I didn’t bring you here so I could complain about work. I have a solution.” 

“Ah, yes. The one that involves your boss and my boss?” 

Kurt nodded, “I think they should date.” And he said it so seriously, soberly, because he really did think they should, that when Blaine laughed, sharp and a bark, anger flicked through him. “What?” 

“I just- wait, you’re serious? Kurt, what?” Blaine shifted in his seat, “Why are you concerned about your boss’ dating life?” 

“I’m not _concerned_ about it.” His voice was tight, “But, I thought that maybe if there was someone she wanted to spend her weekends with, I could get mine back too.” 

“Oh,” Blaine said, and it looked like he understood. “Why Arthur?” 

Now it was Kurt’s turn to shift in his seat, not knowing how much he should say, but he felt a little more at ease now that Blaine knew, got it, seemed to be taking it seriously. “She said something about him last night. I think she’d be interested, were he to show some interest in her.” 

Blaine nodded slowly, “So, we’re setting our bosses up so that Isabelle gets distracted enough that you get your weekends back?” 

“Correct,” Kurt confirmed. “I’m not saying they’re soulmates, but if we can at least get them to have a fling then I can finally go on the date I’ve been trying to go on, and sleep past seven for the first time in over a month.” 

“A date?” 

Kurt wanted to wipe off the goofy grin that was hanging from Blaine’s lips, “Shut up.” 

“All of this is so you can go on a date with some guy?” 

And he was only teasing, Kurt knew he was, but the words dug under his skin and rattled, “He’s not some guy, Blaine. He’s... really sweet, and he’s only one part of the reason for all of this, okay? My skin is suffering the consequences of this schedule she has me on.” 

“Your skin looks fine,” Blaine murmured, and Kurt hated how quiet and earnest it sounded. And then, after a long moment, “I'm in." 

“You’ll help me?” 

“Yes, yes,” Blaine nodded his head, laughing, “Arthur works me pretty hard, too, so it’ll be mutually beneficial. Give me her number and I’ll pass it along.” 

“Oh, no. They can’t know we’re involved.” 

Blaine was finishing off his beer and he narrowed his eyes at Kurt, “Then how on earth are we supposed to-” 

“Don’t worry. I have an idea.” 

* * *

Kurt's not really sure how it worked. 

He had feigned confidence in his idea to Blaine, adamant that it would work, but in reality, he had no idea how it would pan out. But they’re here at the Chris Gelinas Showcase, and so are Isabelle and Arthur, so they must have done something right. 

It had all felt a little silly – organising their plan as if they were in a heist movie and figuring out the logistics. It didn’t help that Blaine had been eager and enthusiastic about it the whole time. He was so goddamn agreeable. It was infuriating. But they’d finally settled on what to do and now Kurt was sitting in the front row of the fashion show waiting to put the plan into action. His knee wouldn’t stop bouncing slightly, up and down, up and down, up and down. 

“Kurt, are you okay?” 

Isabelle looked a little weary. It had taken a lot of persuading masked as casual interest to get her to agree to come. She had resisted, claiming that she always got the most amount of work done on Thursday nights, but Kurt had insisted that this would be the perfect way to clear their heads and get some new inspiration. When he’d framed it like that – to help the showcase – she'd nodded her head slowly and said, “Okay. Okay, yeah. Let’s do it.” 

Blaine had simply put it into Arthur’s schedule. Apparently, he never questioned what was in his calendar and had basically given Blaine complete authority over what went on in his day-to-day life. The lack of interest he seemed to have in his own existence worried Kurt a little bit – Isabelle was headstrong and intelligent and extremely accomplished, and she’d need someone just as competent to keep up with her. He reasoned that if he could run an entire department at Vogue, he must have some talent and drive hidden under all of that schedule ambivalence. Regardless, it got them all in the same room. 

Kurt tried to soothe his leg and smiled at Isabelle, aiming for reassurance. “Yeah, sorry. Just excited for it to start.” It was a weak excuse, but she didn’t push it. 

When there’s only five minutes until the show starts, Kurt tells Isabelle that he’s going to use the bathroom while he still can. Isabelle nods and pulls out her phone, immediately opening the email app. He wants to chastise her about it – they're here to have a good time, not work. But then he remembers that he got her here under work pretenses, and that he’s not actually here to have a good time. He’s here with an ulterior motive. So he just walks to the bathroom silently and hopes that Blaine does his part. 

Blaine doesn’t do his part. 

Or – he tries to. But it goes nothing like how they wanted it to. He had led Arthur over to Isabelle as planned, laughed with her as they realised they all knew each other from work, politely told her that she was in their seats, and over-apologised when she explained that the seats were hers. He’d suggested that Arthur take Kurt’s - “I’m sure he won’t mind, Isabelle. I’ll save him a seat near the back with me,” - and been on his way to do just that when Isabelle had reached out to stop him. 

“Blaine - was it?” He had nodded. “I have so much work to do anyway, why don’t you just take my seat?” 

And he’d been left with nothing to do but smile and thank her, try to sound appreciative, and slide in next to Arthur as Isabelle walked out of the building with purpose and her phone to her ear. 

She’d been calling Kurt, explaining that she had to leave to fix something back at the offices and he’d tried to stop her, but the attempt had been feeble at best. It meant that he already knew they’d been unsuccessful when Blaine pushed into the bathroom and began to explain. 

Kurt followed Isabelle back to the office. Blaine stayed and watched the show with Arthur, no legitimate reason not to. 

And one thing was abundantly clear: their plan definitely did not work. 

* * *

It’s not until the Tuesday of the next week that Kurt finally makes a decision and heads back to Blaine’s desk. He’d had to cancel on Chandler again, he was exhausted from the weekend, and all of the hope he’d been feeling after Blaine had agreed to help set Isabelle and Arthur up together had drained. He had deliriously drafted a resignation letter on Sunday night, so he needs to _do_ something. He needs them to try again. 

“Hi.” 

Blaine was typing something and his fingers didn’t break their rhythm as he looked up and smiled far too wide considering Kurt was already wearing a scowl. “Kurt, hey. How are you?” 

“Why do you get a desk right by the window?” 

The tapping stopped at that and Blaine swiveled his chair until his entire body was facing Kurt. “Overlooking the Hudson, no less,” he said, his smile just as wide as before. 

“Your desk is bigger than mine,” but there’s less bite in that complaint. Almost as if he’s just pointing it out. He wants to be mad at Blaine for saying things that are dripping in pleasantness but are actually mock. He wants to be mad at the way that he seems to get some sort of pleasure out of soaking Kurt’s coldness in warmth, just to piss him off. He wants to be mad, but he’s just too tired. 

“There are a million size jokes going through my head right now, but I’m a professional.” And then he cocks his head, taking in Kurt’s frame. “What’s going on?” 

“We need to try again. With Arthur and Isabelle.” 

For the first time since he'd arrived, Blaine’s smile falls a little and his features become something a little more authentic. “I think we more than proved on Thursday that we’re not cut out for the matchmaking life.” 

Kurt nods, almost chuckles a little bit but he swallows that down before it comes to anything, and digs in further, “I know. But- Blaine, I really need this. Or I need to try, at least. Just once more.” 

“You know, they’re real people with their own minds, Kurt. We can’t force them together if they don’t want to be,” but it’s sort of soft, almost caring, not teasing or tight. Like he’s trying to be gentle. 

And he does know that. He would never force Isabelle to do anything, but if he could just at least make it an option that’s available. Put it on the table. Open the door to it. “I know.” 

“What would we even do?” 

“I have an idea.” 

Blaine smirks, “You said that last time.” 

“And it would have worked if you’d done your part properly.” 

His voice is sharp then, he can feel the slice to it, but Blaine just laughs easily. Kurt cannot figure this man out. It’s as if the meaner he is, the better the reaction he gets. It’s mind-boggling. There’s also a tiny voice in the back of head that’s begging him to be kinder; he wants Blaine to help him, and so surely snapping is counterproductive. 

But it seems there really is no need for Kurt to try niceness, because Blaine sighs happily, as if there’s some sort of affection in his decision, and says, “Okay. One more try.” 


End file.
